High polymer gel and activation method for compounds containing active hydrogen

Abstract

Active hydrogen in an active-hydrogen-containing compound is activated by using a polymer gel having a three-dimensional network structure holding a solvent inside thereof and active sites inside the three-dimensional network structure and surfaces thereof. The ratio of swell of the polymer gel is preferably set to not less than 2, and it is preferable for the polymer gel to have a basic functional group derived from at least one compound selected from the group consisting of tertiary amine compounds, quaternary ammonium salts, cyclic amine compounds and sulfides. The activation of active hydrogen in the active-hydrogen-containing compound is preferably carried out under the condition that the amount of basic active sites of the polymer gel per unit volume in the active system accompanying the activation of active hydrogen is set to not less than 0.43 mmol/cc.

1. An method for addition of a heterocyclic compound or an aldehyde to an active-hydrogen-containing compound, comprising the steps of
 activating an active-hydrogen-containing compound with a polymer gel having a swell ratio of not less than 2 and comprising a cyclic amine structure or a cyclic quaternary ammonium salt structure in the main chain of the polymer in the presence of a heterocyclic compound or an aldehyde under conditions conducive to the addition of the heterocyclic compound or the aldehyde to the active-hydrogen-containing compound.  
 
     
     
       2. The addition method of  claim 1 , wherein:
 the active-hydrogen-containing compound is a compound selected from the group consisting of phenols, amides, alcohols, and carboxylic acids; and  
 the heterocyclic compound is an oxirane compound.  
 
     
     
       3. The addition method of  claim 1 , wherein the polymer gel has a three-dimensional network structure holding solvent inside thereof and also has active sites for activating the active-hydrogen-containing compound inside the three-dimensional network structure and/or on the surface thereof. 
     
     
       4. The addition method of  claim 1 , wherein the cyclic amine structure or the cyclic quaternary ammonium salt structure in the polymer gel is derived from at least one selected from the group consisting of N,N,N-triallylamines, N,N-diallylamines, and diallyldimethylammonium chlorides. 
     
     
       5. The addition method of  claim 1 , wherein the polymer gel has a thermal decomposition temperature, that is, a heat-absorption peak temperature on a TG-DTA curve obtained when the polymer gel is heated at a rate of 5° C./min in a nitrogen gas flow, of not less than 300° C. 
     
     
       6. The addition method of  claim 1 , wherein:
 the active-hydrogen-containing compound is (meth)acrylic acid and the heterocyclic compound is an oxirane compound, and  
 the (meth)acrylic acid is activated with the polymer gel under conditions conducive to the addition of the oxirane compound to the (meth)acrylic acid, so as to form a hydroxyalkyl(meth)acrylate.  
 
     
     
       7. The method of  claim 1 , wherein the active-hydrogen-containing compound is a carboxylic acid. 
     
     
       8. The method of  claim 1 , wherein the active-hydrogen-containing compound is an unsaturated carboxylic acid. 
     
     
       9. The method of  claim 1 , wherein the active-hydrogen-containing compound is acrylic acid. 
     
     
       10. The method of  claim 1 , wherein the active-hydrogen-containing compound is a phenol or a derivative thereof. 
     
     
       11. The method of  claim 1 , wherein the heterocyclic compound is an oxirane. 
     
     
       12. The method of  claim 1 , wherein the heterocyclic compound is ethylene oxide. 
     
     
       13. The method of  claim 1 , wherein the polymer gel is a copolymer of N,N-diallylamine hydrochloride and N,N,N-triallylamine hydrochloride. 
     
     
       14. The method of  claim 1 , wherein
 active-hydrogen-containing compound is acrylic acid;  
 the heterocyclic compound is ethylene oxide; and  
 the polymer gel is a copolymer of N,N-diallylamine hydrochloride and N,N,N-triallylamine hydrochloride.  
 
     
     
       15. The addition method of  claim 1 , wherein the polymer gel has a ratio of swell in a range of 2.5 to 10. 
     
     
       16. The addition method of  claim 1 , wherein the polymer gel has a ratio of swell in a range of 3 to 8.